#Operations 3: What Ops Pros Can Learn from this $9 Billion Company

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This is a podcast episode titled, #Operations 3: What Ops Pros Can Learn from this $9 Billion Company. The summary for this episode is: Today on #Operations, host Sean Lane sits down with Okta's VP of Business Operations, Jake Randall. Okta's market cap is now $9 billion...not a bad company to learn from. Together Sean and Jake discuss how to actually measure your ops team's performance, scaling through hypergrowth, Jake's career path at Okta, what he's reading now and much more.

Sean Lane: Hey everyone, Sean Lane here. Welcome back for another episode of Operations, the show where we look under the hood of companies in hyper growth. You know how in sales you can always tell pretty much exactly where someone is at in terms of their performance? You look at percentage of attainment to quota and by and large, you have your answer, right? In a lot of other gigs, though, including operations, the answer to how, quote- unquote," good" someone is at their job, can be a little bit murkier, and how good an operations team is can be murkier still. Luckily, on today's episode, our guest Jake Randall from Okta, is going to help us clear things up. You're also definitely going to want to stick around for one hell of a pivot table metaphor from Jake coming up later in the show. That may be the nerdiest sentence I've ever said out loud. Anyways, Jake is the VP of Operations at Okta, and he's had a front row seat for nearly all of the stages of hyper- growth during his seven plus years at the company, from around their series B up through when the company went public last year and beyond. By the way, Okta now has a$ 9 billion market cap, that's billion with a B. During his time at the company, Jake has risen through the ranks in a variety of different finance and BizOps roles. Now, because everyone has their own slightly different definition, before we jumped in, I wanted to level set with Jake on what BizOps actually means at Okta.

Jake Randall: Yeah, it's a great question, I think. Whenever I meet someone who has a similar title as myself, first question is," Wait, so what do you actually do?" Which is, I think somewhat unique, maybe, in the BizOps world. So, I think Okta has a slightly, maybe, different version of it, ourselves. BizOps at Okta is really, I'll call it a centralized strategy and operations team. And so, that's everything, really, for a product to go- to- market org. That's everything from how we think about building pipeline, all the way through to renewing our customers. So, think full customer life cycle, and then, basically supporting all the teams that are involved in that customer life cycle process. And so, I think the easiest way to think about it is that a big part of your hyper growth company is a sales ops function, or sales strategy. Again, that's actually another role that means different things at other companies. But there's no sales strategy or sales operations that rolls into sales. Sales strategy and operations rolls up into BizOps, and then I report them to our president and help make sure that that entire go- to- market org, and that's the same for all the different ops and strategy functions, support the go- to- market team, so making sure that's all aligned, and working smoothly, and there's a coherent plan.

Sean Lane: Got it. And seven years is a long time, in the tech world, at least, for being in a single place, in a single company. And so, you have also been someone who's been able to grow in your role and responsibility during that time there. And so, for people like me and people who are listening who want to try to grow their careers in ops, why do you think that you've been able to make those jumps and continue to grow inside of ops?

Jake Randall: Yeah, sure. That's a good question. First of all, what I'll say, and I'm sure we'll touch on this, is that I joke that I've worked at 10 different companies over the last seven years, but they all just happened to be the same name. So, that's part of the fun part about as you go through these different spurts. I'm hoping no stops, just spurts.

Sean Lane: Absolutely.

Jake Randall: I think I can give you my background quickly, actually, if that helps. So, I started out the first four years that I was at Okta, for the first four of seven, I ran finance, operations, and legal for us, and then transitioned over the last three years into this BizOps function that I just talked about. I think there's a lot of different things that make you good at ops, or what's been helpful. For me, there was a lot of it that was because of the function and because it is so centralized and you could argue that part of what those offices at Okta, at least, count as connective tissue for the whole business. That puts you in a really strong position to really understand the way, I guess maybe this is why they call it BizOps, the way the business operates. And this is what I tell people on my team, because I think it's certainly how I thought about it in my career of years, that I'm going to put you, as someone on the BizOps team at Okta, I'm going to put you in a great position, where you have incredible insight into the business, how it works, what are our key strategies, what's going on, and then it's really on you to take advantage of that opportunity. And I think that that's something that's for people that are in ops function, you have a unique seat at the table to understand what's happening, and it's really on you to take advantage of that opportunity.

Sean Lane: When Jake talks about taking advantage of an opportunity at a high growth company, I wanted to better understand what that actually means through the lens of ops roles. What does it mean to be, quote," good" at ops? He clearly had navigated that well himself at Okta. And what he told me may surprise you. He said it's actually not just about being analytical or good with numbers or Excel spreadsheets.

Jake Randall: Yeah. I think a lot of what makes people successful in their role is that empathy for the different people that they support and being able to communicate what, at times, can be hard things, either in that they're technical, or very analytical, or hard things in that, if you're in a sales ops role, one of the classic things is comp plans. Those are hard conversations. And the ability to take that analytical mindset and translate it into an empathetic conversation with your business partner, with the head of sales, with the head of marketing and effect change. I think that's actually the most important thing, that you have to be seen as someone that can get out from behind the Excel spreadsheet, as it may be.

Sean Lane: Right. Yeah, that's what I was just going to say." Okay, I want to be empathetic, I want to do that. How do I do that?" I think a lot of that does come from just getting out from behind your desk, or your spreadsheet, whatever it is you want to say, and actually getting out there and having a real perspective on what those people are doing. And I would imagine that during those first few years, when you were doing finance and legal and things like that, that gave you a pretty unique perspective that, I would assume, correct me if I'm wrong, that helps you in your job today?

Jake Randall: Yeah, absolutely. I mean, I think the one that was probably most important was that legal function. As a caveat, I'm not a lawyer. What's the saying?

Sean Lane: Disclaimer, we got it.

Jake Randall: What are those ads? It's like," I'm not a doctor, but I stayed at a Holiday Inn," or something like that. Remember those ads?

Sean Lane: Oh, yeah. Yeah. I think so. Yeah."I stayed at Holiday Inn last night."

Jake Randall: So anyways, as is the nature of any good startup, people get to do lots of things that they shouldn't otherwise be doing. So one of those things for me was running our legal team. And I somehow convinced, actually, a really great legal team that's still here to come on board to help me with that. But part of that was that because of that function, I would go on site with our Chief Revenue Officer, and I was somewhat his right- hand person helping to work through these complex contracts and book commercial negotiations. I actually still own our deal desk here, so pricing, and packaging, and deal structuring for the commercial parts that involves the legal parts to getting some of our largest, most important companies when we were in that series C, series D round, when you're looking to get some momentum going. So things like that, again, I think that's probably somewhat of a unique experience, quite frankly, that I got here.

Sean Lane: Building those connections that Jake is talking about, whether they be with sales, marketing, customer success, that is one of my favorite parts of my job. Let's face it. Even if you're not in ops, the way you're perceived by the people you work most closely with is going to have an impact on how much of an impact you can make. Where things get more interesting, though, is that in ops, you can't just spend all your time developing relationships with people outside your team. You have to spend time with your own team and you have to think about them as well. So I wanted to learn how Jake had set his team up for success.

Jake Randall: So the way we're organized is I'm actually the only person that has BizOps in my title. So I have a head of deal desk, I have a head of sales strategy and operations, I have a head of partners, I've got a head of professional services and customer success, but they all... I think what's really key is that, I guess the point of this connective tissue, is making sure that everyone understands the other parts of the business. And in turn, I think that's a lot of what, as a leader of BizOps, is trying to focus on, is that you may be in charge of deal desk, because we were talking about that, but you'd have to really understand the sales strategy side of business, and you'd have to understand the professional services side of the business. Because what you're really trying to do is create an efficient go- to- market. And so, just finding those connection points, understanding people that have this basically having a team, I guess, that can work to find those points, and therefore figure out how to create efficiencies and how to create that kind of scale and leverage. That's a lot of what BizOps is doing, is trying to create scale and leverage for the business. And so people that think outside the box, people that think outside their functioning is really critical.

Sean Lane: Finding connection points to create scale and leverage. If you take nothing else away from Jake's team today, it's that. Finding connection points to create scale and leverage. But I wanted to illustrate this point further, so let's dig into an example. Pipeline.

Jake Randall: Yeah. Marketing does a ton of pipeline build for us. But when we think about pipeline, it's not a marketing thing. There's partners that bring us into deals. There's AEs that can do outbound. There's customer success reps that can find the cross sell when they're in there doing the QBR with all of our existing customers. And so it's really also, it's funny to make jokes about Excel and whatnot, but we've always thought of it as a pivot table. Because it's an ops podcast, ops people will all know what that is, right?

Sean Lane: Yeah. I think we've got the right audience.

Jake Randall: Most people know what a pivot table is in general. But it's this ability to take the idea of marketing, and sales, and all these what historically have been at times siloed functions and their own kind of thing, and how can you pivot that, and look at it differently, and say it's not about marketing, or sales, or partners, or whatever it may be, but it's about how do we generate demand in our business. And that's a much bigger, broader, interesting way to think about it, in my opinion, because you're thinking about how do we all work together? How do we all play a part in this broader concept of building pipeline or building demand? And so I think that's a lot to what I try to think about with the team. And I think how we've thought about it in general over time is shift the lens on how you look at some of these common problems.

Sean Lane: Yeah. So let me just regurgitate that back to you, because I think this is an awesome takeaway and I want to make sure that I'm getting it right. But basically, you're thinking about ops as that pivot table where you can give the right lens back to not only those key stakeholders that traditionally you might think," Okay, marketing cares most about pipeline," but instead, using that as a lens to be able to make it more of a company metric or a company topic and get alignment around that thing?

Jake Randall: Absolutely. Yeah. So you said it much better than I did, but that's absolutely the idea, that there's pillars, I'll call it, of how you go- to- market, if ultimately, I would call BizOps an office of your go- to- market strategy and operations. There's pillars of that go- to- market strategy, and we need to get everyone to feel some ownership in that. So again, pipeline, well, that's something that everyone should feel ownership in, and that we should all orient around that, and not make it," Hey, marketing, you're not generating enough pipeline." Because it's not just marketing. AEs, you should do pipeline gen, and we should have a common framework to look at that and think about how do we generate demand across all of these different business units. Similarly, you can think about forecasting. That's traditionally a sales process. You all get on a call and you do forecasting. Well, we've tried to do a lot to make it really about how does everyone have some ownership in that? How do you make sure that sales forecasting is also about building pipeline? So let's get marketing involved. Let's get partners involved. Let's think about different ways to really shift that lens and fix a common issue.

Sean Lane: And I think for people that are listening to this, I think you're going to have two big buckets. You're going to have people like me who are lucky enough to work on a centralized ops team like the one that you're talking about, and I'm nodding aggressively at the things that you're saying. And then there's also going to be some folks who are hearing that and they're going to be shaking their heads because either they don't buy into this idea or they're in a particular organization where they feel incredibly siloed and they would like to be in a world where some of these things are looked at more comprehensively and across that entire customer journey that you started the conversation by talking about. For the people in that second bucket, how can they try to enact some sort of change or shift some of those lenses that we're talking about, so that their companies can look at things similar to the way that you do at Okta? Does that make sense?

Jake Randall: Yeah, that makes all sense. First of all, I'll say that I don't know if the way we do or the way Drift does it is correct. But all I know is we have a much better plan. I mean, I joke at times. If it was easy, if there was a common playbook that worked for everyone, then every company would go public. There's always challenges. But I think that it's interesting, a little bit to what I talked about maybe earlier around people that want to go and do something different and want to expand. I think that one of the things I talk about with my team, certainly, is that there's tons of problems. Every company has lots of problems. God knows that the majority of my job at this point has turned into people just calling me with problems. No one ever calls me with good things. Everyone always just calls to say," I want to tell you how messed up this is." No one ever calls me and says," This is working perfectly." But there's always problems.

Sean Lane: Thank you so much. You're doing a hell of a job.

Jake Randall: Yeah. Yeah, no. It's like,"Hey, this is broken. What's happening here?" But there's always problems. And one of the things that I joke about is that everyone's actually just looking for someone to show up with a PowerPoint and explain how we can fix it. And what you find, I think, and this is a little bit of what makes someone successful in BizOps, back to the earlier conversation, people are actually pretty open and welcome to new ideas, and you'll never get, assuming you work at a good company with a good culture and a good boss, you're never going to get in trouble for showing up with a new idea and a new way to look at things. And if you can say," Hey, this is a problem. Here's why this is impacting us in this way. Here's a potential solution to it," quite frankly, that's what everyone wants. That's the dream. If you're a manager, and you walk into your one- on- one, and someone shows up to their one-on- one and says," Hey, I was thinking about this issue, and here's my thoughts onto how we could fix it, and here's how it would work, and here's whatever. Here's why, here's some fancy PowerPoint or something that I was up late last night putting together for you," you're like," Yes." There's no greater moment in your time as a manager than that moment. And so, I think people can be scared, understandably. There's this,"Oh, I'm putting myself out there. I'm going to put my neck on the line. I'm going to offer up something new and different than what we've done in the past." But I think you should just feel... If you actually believe that's the right thing to do, you should feel confident in that. And I would also just encourage people that are listening, that's what everyone wants.

Sean Lane: For someone to show up with the answers.

Jake Randall: That's the whole thing. It's like, someone show up and say," Hey, I think we can do it this way. And wouldn't this be cool?" And then you should be... It might not work. God knows I've come up with ideas that people were like," That's a terrible idea. What were you thinking?" But I never get in trouble for coming with a... You should never feel anxious around asking about it or proposing it. So I think it's really just being comfortable with that and thinking about how to... Again, if you're in an ops function, you probably have great purview over the business. You can see these issues. And so, take comfort in the fact that people are actually looking to try to bring these things to light and propose new solutions.

Sean Lane: Right. And I think half the battle on that, too, is just realizing that you do have that purview, and taking a step back and realizing the fact that you have this exposure that is unique and you have a perspective that is unique. I feel very lucky that I get to have conversations like this as a result of doing this show. But I also think one of the reasons why we wanted to do it was the fact that I personally, at least, and maybe I'm not looking hard enough, couldn't find a lot of resources that were like this out there for ops specific people. And I'm curious, am I wrong? Where do you go to try and get better?

Jake Randall: That's a great point. Now I'm kind of racking my brain. What resources are out there? I'll tell you that I agree. There's not a lot of resources out there like this. I've gone to happy hours or whatever. I think a lot of the shared resources become networking, I guess, within this sub- industry, or whatever you would call it, that we do. I think what's funny about it is there is, at least my own take on it, or what I've seen, is there's lots of resources out there around how to think about setting a pipe gen target. Lots of resources about how to run a forecast call, or what cadence you should set up as a sales ops team, or how to think about different ways to affect churn or whatever it may be, if you want to think through the entire customer life cycle there. Those are all very tactical things, which are super important, and there's stuff out there. But I think the idea of how do you look at it more broadly, which I think is, again, this idea of, again, BizOps, and it seems to be more where the operations function is trending over time, there's not a lot out there around that. So I think it's a super interesting topic. I might put something together on it.

Sean Lane: Before we go, at the end of each show, we're going to ask each guest the same lightning round of questions. Here we go. Best book you've read in the last six months?

Jake Randall: I just read a book called Arsenal of Democracy, which is about the industrialization of America to get ready for World War II, so you can tell that I like operations teams.

Sean Lane: Cool.

Jake Randall: It's like Ford, and the production plants, and heavy operations history stuff. So yeah. There you go.

Sean Lane: You passed the test.

Jake Randall: Yeah.

Sean Lane: What is your favorite part about working in ops?

Jake Randall: It's, you can probably guess this also, given what we just talked about, but it's just all the exposure that you get. It's the people that you get to talk to and meet and the way you get to solve problems across the business.

Sean Lane: Least favorite part about working in ops?

Jake Randall: All the problems that there are to solve and all the bad conversations you have.

Sean Lane: Someone who impacted you getting the job you have today?

Jake Randall: So, the way I got my job, actually, there's a woman, Julie. I was actually in Boston. I grew up in Boston, where Drift is, and I was working for a healthcare startup. And when we were, quite frankly, winding down this healthcare startup, it turns out that there's failures, it's okay to fail and eventually you'll have success. We were winding down this healthcare startup, and I decided that I wanted to keep doing startups, despite the lack of success in this healthcare one I was doing in Boston. And this woman Julie was like," Oh, you should talk to my friend, Todd." Todd is our CEO. And she said," Oh, you should talk to my friend Todd if you want to keep doing startups." He just started this startup, and she was friends with him. And so she introduced me, and I call her up, and I'm like," You realize your friend Todd is pretty smart, and they just raised their A, their first cloud investment of Andreessen Horowitz. And they just had their B with like Greylock. This is not just somebody that's kicking around in a garage." She was like,"I don't know. He's just my friend. We used to go out drinking or whatever in San Francisco when I lived there." And I was like," Yeah." So probably Julie, the most, right?

Sean Lane: That is an amazing intro. I hope that she gets a big thank you. All right. Last one. One piece of advice for people who want to have your job someday?

Jake Randall: Don't be afraid to just put yourself out there, I think. To what I was talking about earlier, again, it's that you've got to take some risks. You've got to take a stance and have an opinion on things and come up with some solutions and just own it. I think that you have to put yourself outside your comfort zone. So don't be afraid to do that.

Sean Lane: All right. That's it. A huge thank you to Jake Randall from Okta for joining us for this episode of Operations, and an equally enormous thank you to all of you for tuning in. I want to just take a minute and thank everyone in the Seeking Wisdom community who sent me a LinkedIn message, tweeted at me after we've launched the first couple episodes. The response has been amazing. Special shout out to Maribel from PI. Denis sent me a LinkedIn message from PandaDoc. Ashley from Notarize. Matt Woods sent me a video reply on Twitter, which was really cool. I had never seen that before. All the feedback has been overwhelmingly positive. Also good to have some critics. I got a text from my mom. She wanted to make sure that we take a look at the background music again. She texted me," Any chance the background music could be more upbeat and inviting?" So we will work on that. You can't please everybody. Anyways, whether you've got feedback on the music or you have some guests that you want to hear from or topics you want us to hear us cover, please help us make this show better. Send me your feedback. Shoot me a note on LinkedIn. Tweet at me @ Seany_Biz. Or you can always leave us one of those coveted six star reviews on Apple Podcasts. Six star reviews only, please. That's it for me. See you guys next time.


Today on #Operations, host Sean Lane sits down with Okta's VP of Business Operations, Jake Randall. Okta's market cap is now $9 billion...not a bad company to learn from. Together Sean and Jake discuss how to actually measure your ops team's performance, scaling through hypergrowth, Jake's career path at Okta, what he's reading now and much more.